IE61955B1 - "3-(2-Haloalkyl)-1,4-oxathiins and 2-(2-haloalkyl)-1,4-dithiins, and treatment of leukemia and tumors therewith" - Google Patents
"3-(2-Haloalkyl)-1,4-oxathiins and 2-(2-haloalkyl)-1,4-dithiins, and treatment of leukemia and tumors therewith"Info
- Publication number
- IE61955B1 IE61955B1 IE59788A IE59788A IE61955B1 IE 61955 B1 IE61955 B1 IE 61955B1 IE 59788 A IE59788 A IE 59788A IE 59788 A IE59788 A IE 59788A IE 61955 B1 IE61955 B1 IE 61955B1
- Authority
- IE
- Ireland
- Prior art keywords
- oxathiin
- hydrogen
- haloalkyl
- methyl
- test
- Prior art date
Links
- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 24
- 208000032839 leukemia Diseases 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052717 sulfur Chemical group 0.000 claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000011593 sulfur Chemical group 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 3
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 230000001939 inductive effect Effects 0.000 claims description 2
- CPRVXMQHLPTWLY-UHFFFAOYSA-N 1,4-oxathiine Chemical compound O1C=CSC=C1 CPRVXMQHLPTWLY-UHFFFAOYSA-N 0.000 claims 6
- AKAIWNDBVZJOAJ-UHFFFAOYSA-N 1,4-dithiine Chemical compound S1C=CSC=C1 AKAIWNDBVZJOAJ-UHFFFAOYSA-N 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000012010 growth Effects 0.000 abstract description 6
- 150000002367 halogens Chemical group 0.000 abstract description 5
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 46
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
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- 206010006187 Breast cancer Diseases 0.000 description 2
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- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- OMQHDIHZSDEIFH-UHFFFAOYSA-N 3-Acetyldihydro-2(3H)-furanone Chemical compound CC(=O)C1CCOC1=O OMQHDIHZSDEIFH-UHFFFAOYSA-N 0.000 description 1
- OZEKTIKQEZYCJF-UHFFFAOYSA-N 3-acetyl-3-chloro-5-ethyloxolan-2-one Chemical compound CCC1CC(Cl)(C(C)=O)C(=O)O1 OZEKTIKQEZYCJF-UHFFFAOYSA-N 0.000 description 1
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- 238000011719 B6C3F1 mouse Methods 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- LHKAYYBHYUKGOK-UHFFFAOYSA-N CC(CCCCC)=O.ClCCC(C(CCC)=O)Cl Chemical compound CC(CCCCC)=O.ClCCC(C(CCC)=O)Cl LHKAYYBHYUKGOK-UHFFFAOYSA-N 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
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- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000004969 haloethyl group Chemical group 0.000 description 1
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- 239000007972 injectable composition Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
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- YBKGERLDRMINOV-UHFFFAOYSA-N oxathiine Chemical compound O1SC=CC=C1 YBKGERLDRMINOV-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2465787A | 1987-03-11 | 1987-03-11 | |
| US07/146,512 US4822813A (en) | 1987-03-11 | 1988-01-21 | 3-(2-Haloalkyl)-1,4-oxathiins and 2-(2-haloalkyl)-1,4-dithiins, and treatment of leukemia and tumors therewith |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE880597L IE880597L (en) | 1988-09-11 |
| IE61955B1 true IE61955B1 (en) | 1994-11-30 |
Family
ID=26698721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE59788A IE61955B1 (en) | 1987-03-11 | 1988-03-03 | "3-(2-Haloalkyl)-1,4-oxathiins and 2-(2-haloalkyl)-1,4-dithiins, and treatment of leukemia and tumors therewith" |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4822813A (de) |
| JP (1) | JPS63264580A (de) |
| AT (1) | AT397089B (de) |
| AU (1) | AU597478B2 (de) |
| BE (1) | BE1002181A3 (de) |
| CA (1) | CA1320210C (de) |
| CH (1) | CH674366A5 (de) |
| DE (1) | DE3808024A1 (de) |
| DK (1) | DK168707B1 (de) |
| ES (1) | ES2011075A6 (de) |
| FR (1) | FR2612188B1 (de) |
| GB (1) | GB2201958B (de) |
| GR (1) | GR1000238B (de) |
| IE (1) | IE61955B1 (de) |
| IL (1) | IL85517A (de) |
| IT (1) | IT8819726A0 (de) |
| LU (1) | LU87152A1 (de) |
| NL (1) | NL8800531A (de) |
| NZ (1) | NZ223798A (de) |
| SE (1) | SE466400B (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9001327D0 (en) * | 1990-01-19 | 1990-03-21 | May & Baker Ltd | New compositions of matter |
| IL103586A (en) * | 1991-10-30 | 1997-09-30 | Astra Ab | Process for the preparation of 4-methyl-5- (2-chloroethyl)-thiazole and analogues thereof |
| CN106278845B (zh) * | 2016-05-19 | 2019-03-05 | 海正化工南通有限公司 | 一种3,5-二氯-2-戊酮的合成工艺 |
| CN106565441A (zh) * | 2016-11-10 | 2017-04-19 | 安徽国星生物化学有限公司 | 一种3,5‑二氯‑2‑戊酮的合成方法 |
| CN106673978B (zh) * | 2016-11-30 | 2019-06-25 | 湖南化工研究院有限公司 | 3,5-二氯-2-戊酮的连续化合成方法 |
| CN107473949B (zh) * | 2017-09-26 | 2020-10-02 | 安徽国星生物化学有限公司 | 一种3,5-二氯-2-戊酮的合成工艺 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3868459A (en) * | 1968-05-21 | 1975-02-25 | Aquitaine Petrole | Method of killing nematodes using certain halomethyl oxathienes |
| US3728357A (en) * | 1970-09-08 | 1973-04-17 | Uniroyal Inc | 2-(substituted-methyl)-5,6-dihydro-1,4-oxathiin-3-carboxamides |
| US4319003A (en) * | 1980-09-26 | 1982-03-09 | General Motors Corporation | Poly(methyl methacrylate) polycarbonate block copolymers |
-
1988
- 1988-01-21 US US07/146,512 patent/US4822813A/en not_active Expired - Lifetime
- 1988-02-23 IL IL85517A patent/IL85517A/xx not_active IP Right Cessation
- 1988-02-25 GB GB8804454A patent/GB2201958B/en not_active Expired - Fee Related
- 1988-03-02 NL NL8800531A patent/NL8800531A/nl not_active Application Discontinuation
- 1988-03-03 IE IE59788A patent/IE61955B1/en not_active IP Right Cessation
- 1988-03-08 NZ NZ223798A patent/NZ223798A/xx unknown
- 1988-03-08 CH CH869/88A patent/CH674366A5/de not_active IP Right Cessation
- 1988-03-08 GR GR880100136A patent/GR1000238B/el unknown
- 1988-03-09 LU LU87152A patent/LU87152A1/fr unknown
- 1988-03-09 CA CA000560945A patent/CA1320210C/en not_active Expired - Fee Related
- 1988-03-09 AU AU12827/88A patent/AU597478B2/en not_active Ceased
- 1988-03-10 BE BE8800274A patent/BE1002181A3/fr not_active IP Right Cessation
- 1988-03-10 DE DE3808024A patent/DE3808024A1/de not_active Withdrawn
- 1988-03-10 DK DK131188A patent/DK168707B1/da not_active IP Right Cessation
- 1988-03-10 SE SE8800863A patent/SE466400B/sv not_active IP Right Cessation
- 1988-03-10 FR FR888803118A patent/FR2612188B1/fr not_active Expired - Lifetime
- 1988-03-10 JP JP63055123A patent/JPS63264580A/ja active Granted
- 1988-03-10 IT IT8819726A patent/IT8819726A0/it unknown
- 1988-03-11 AT AT0067688A patent/AT397089B/de not_active IP Right Cessation
- 1988-03-11 ES ES8800731A patent/ES2011075A6/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63264580A (ja) | 1988-11-01 |
| NL8800531A (nl) | 1988-10-03 |
| IL85517A0 (en) | 1988-08-31 |
| SE8800863D0 (sv) | 1988-03-10 |
| IL85517A (en) | 1992-09-06 |
| GB2201958A (en) | 1988-09-14 |
| SE8800863L (sv) | 1989-09-12 |
| IE880597L (en) | 1988-09-11 |
| AU1282788A (en) | 1988-09-15 |
| FR2612188B1 (fr) | 1991-02-15 |
| FR2612188A1 (fr) | 1988-09-16 |
| LU87152A1 (fr) | 1988-11-17 |
| AT397089B (de) | 1994-01-25 |
| BE1002181A3 (fr) | 1990-10-02 |
| DK168707B1 (da) | 1994-05-24 |
| GR880100136A (en) | 1989-01-31 |
| CH674366A5 (de) | 1990-05-31 |
| DK131188A (da) | 1988-09-12 |
| DE3808024A1 (de) | 1988-09-22 |
| ES2011075A6 (es) | 1989-12-16 |
| DK131188D0 (da) | 1988-03-10 |
| US4822813A (en) | 1989-04-18 |
| AU597478B2 (en) | 1990-05-31 |
| JPH0372221B2 (de) | 1991-11-18 |
| CA1320210C (en) | 1993-07-13 |
| NZ223798A (en) | 1989-12-21 |
| IT8819726A0 (it) | 1988-03-10 |
| ATA67688A (de) | 1993-06-15 |
| GR1000238B (el) | 1992-05-12 |
| GB2201958B (en) | 1990-10-10 |
| SE466400B (sv) | 1992-02-10 |
| GB8804454D0 (en) | 1988-03-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |